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维基百科

熊果酸

一月 01, 1970

熊果酸（英语：Ursolic acid，也译为乌索酸，3-β-羟基-熊果-12-烯-28-羧酸，3-beta-3-hydroxy-urs-12-ene-28-oic-acid）是一种五环三萜物质，最早在1920年发现于苹果的表皮蜡质中。熊果酸也存在于许多植物的果皮中以及迷迭香、麝香草等草药中。

Ursolic acid
IUPAC名
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid[1]
系统名
(1R,2S,5S,8R,9S,10S,14R,15R,18S,20R)-18-hydroxy-1,2,8,9,15,19,19-heptamethylpe ntacyclo[12.8.0.02,11.05,10.015,20]docos-11-ene-5-carboxylic acid
(1R,2S,5S,8R,9S,10S,14R,15R,18S,20R)-1,2,8,9,15,19,19-七甲基-18-羟基五环[12.8.0.02,11.05,10.015,20]-11-二十二烯-5-甲酸
别名 Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid[1]
识别
CAS号 77-52-1  Y
PubChem 64945
ChemSpider 58472
SMILES
 
  • O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)[C@@H](C)[C@H](C)CC5
InChI
 
  • 1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
InChIKey WCGUUGGRBIKTOS-GPOJBZKABB
ChEBI 9908
性质
化学式 C30H48O3
摩尔质量 456.7 g·mol−1
熔点 285 - 288 °C（270 K）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

自然发生 编辑

熊果酸存在于许多植物，如紫茉莉[2]以及日常生活中使用的许多水果和草药（例如苹果、罗勒、越桔、蔓越莓、接骨木花、薄荷、迷迭香、薰衣草、牛至、百里香、山楂和李子）中。苹果皮含有大量的熊果酸以及相关化合物。 [3]

潜在的生物化学作用 编辑

已经研究了熊果酸的许多潜在生化作用，但是没有临床研究表明它对人类健康有益。在体外，熊果酸通过抑制STAT3激活途径抑制各种类型癌细胞的增殖，[4] [5]并且还可以减少癌细胞的增殖并诱导细胞凋亡。 [6]熊果酸也已显示能抑制JURK白血病T细胞的JNK表达和IL-2活化，导致增殖和T细胞活化的减少。[7]熊果酸是一种弱芳香酶抑制剂（IC50 = 32μM），[8]并且已经显示当添加到喂养给小鼠的饮食中时增加肌肉和棕色脂肪的量并减少白色脂肪肥胖和相关病症。 在生理浓度下，熊果酸还诱导了eryptosis（有缺陷的红细胞中的类似凋亡的细胞自杀死亡）。 [9]已经发现它可以减少肌肉萎缩并刺激小鼠的肌肉生长，也显示出潜在的心脏保护作用。 [10]

在小鼠中，熊果酸在坐骨神经损伤后诱导神经再生。[11] 熊果酸可改善多摩酸诱导的小鼠认知功能障碍。[12] 熊果酸可通过阻断内质网应激和IκB激酶β/核因子-κB介导的炎症通路来改善高脂饮食引起的认知障碍。 [13] 熊果酸通过抑制p38 /NF-κB介导的炎症途径减轻脂多糖诱导的小鼠大脑认知功能障碍。[14] 熊果酸可改善认知障碍并减轻D-半乳糖诱导的衰老小鼠大脑中的氧化损伤。[15]熊果酸可促进部分肝切除术后小鼠肝脏的再生。 [16]在以高脂饮食喂养的链脲佐菌素诱导的糖尿病小鼠中，熊果酸可增强细胞免疫系统和胰腺β细胞功能。[17]UA增加骨骼肌质量，以及握力和运动能力。 增强耐力，减少与肌肉萎缩发展有关的基因的表达，并减少累积疲劳和运动引起的压力的指标。 [18]

在大鼠中，熊果酸改善了高脂饮食诱导的肝脂肪变性，并改善了高脂饮食诱导的非酒精性脂肪肝疾病的代谢紊乱。 [19]

用途 编辑

熊果酸可以在用于化妆品添加剂的植物中发现。 熊果酸可以作为合成更有效的生物活性衍生物的起始材料，例如实验性抗肿瘤剂。 [20]

请参见 编辑

参考文献 编辑

  1. ^ 1.0 1.1 CID 64945 from PubChem
  2. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract （页面存档备份，存于互联网档案馆）)
  3. ^ Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties. Food Chem. April 2017, 220: 477–489. PMID 27855928. doi:10.1016/j.foodchem.2016.10.029. 
  4. ^ Ursolic acid inhibits nuclear factor-kappaB activation induced by carcinogenic agents through suppression of IkappaBalpha kinase and p65 phosphorylation: correlation with down-regulation of cyclooxygenase 2, matrix metalloproteinase 9, and cyclin D1 (PDF). Cancer Res. 2003, 63 (15): 4375–83 [2020-03-02]. PMID 12907607. （原始内容 (PDF)于2013-02-21）. 
  5. ^ Pathak AK; Bhutani M; Nair AS; et al. Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells. Mol. Cancer Res. 2007, 5 (9): 943–55. PMID 17855663. doi:10.1158/1541-7786.MCR-06-0348. 
  6. ^ Wang X, Zhang F, Yang L, Mei Y, Long H, Zhang X, Zhang J, Qimuge-Suyila, Su X.,"Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo", J Biomed Biotechnol. 2011;2011:419343 Full-text pdf （页面存档备份，存于互联网档案馆）
  7. ^ Kaewthawee, Narawan; Brimson, Sirikalaya. The Effects of Ursolic Acid on Cytokine Production via the MAPK Pathways in Leukemic T-Cells (PDF). EXCLI. February 2013, 12 (February): 102–114 [2020-03-02]. （原始内容 (PDF)于2013-05-25）. 
  8. ^ Gnoatto, SC; Dassonville-Klimpt, A; Da Nascimento, S; Galéra, P; Boumediene, K; Gosmann, G; Sonnet, P; Moslemi, S. Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. European Journal of Medicinal Chemistry. 2008, 43 (9): 1865–77. PMID 18192087. doi:10.1016/j.ejmech.2007.11.021. 
  9. ^ Triggering of erythrocyte cell membrane scrambling by ursolic acid. J Nat Prod. 2011, 74 (10): 2181–2186. PMID 21923134. doi:10.1021/np2005133. 
  10. ^ Uncoupling and antioxidant effects of ursolic acid in isolated rat heart mitochondria. J. Nat. Prod. July 2011, 74 (7): 1640–4. PMID 21648406. doi:10.1021/np200060p. 
  11. ^ Liu, Biao; Liu, Yan; Yang, Guang; Xu, Zemin; Chen, Jiajun. Ursolic acid induces neural regeneration after sciatic nerve injury. Neural Regeneration Research. 2013-09-25, 8 (27): 2510–2519. ISSN 1673-5374. PMC 4145935  . PMID 25206561. doi:10.3969/j.issn.1673-5374.2013.27.002. 
  12. ^ Wu, Dong-mei; Lu, Jun; Zhang, Yan-qiu; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Li, Meng-qiu. Ursolic acid improves domoic acid-induced cognitive deficits in mice. Toxicology and Applied Pharmacology. 2013-09-01, 271 (2): 127–136. ISSN 1096-0333. PMID 23707761. doi:10.1016/j.taap.2013.04.038. 
  13. ^ Lu, Jun; Wu, Dong-mei; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Shan, Qun. Ursolic acid improves high fat diet-induced cognitive impairments by blocking endoplasmic reticulum stress and IκB kinase β/nuclear factor-κB-mediated inflammatory pathways in mice. Brain, Behavior, and Immunity. 2011-11-01, 25 (8): 1658–1667. ISSN 1090-2139. PMID 21708244. doi:10.1016/j.bbi.2011.06.009. 
  14. ^ Wang, Yong-Jian; Lu, Jun; Wu, Dong-mei; Zheng, Zi-hui; Zheng, Yuan-Lin; Wang, Xiao-hui; Ruan, Jie; Sun, Xiao; Shan, Qun. Ursolic acid attenuates lipopolysaccharide-induced cognitive deficits in mouse brain through suppressing p38/NF-κB mediated inflammatory pathways. Neurobiology of Learning and Memory. 2011-09-01, 96 (2): 156–165. ISSN 1095-9564. PMID 21496491. doi:10.1016/j.nlm.2011.03.010. 
  15. ^ Lu, Jun; Zheng, Yuan-Lin; Wu, Dong-Mei; Luo, Lan; Sun, Dong-Xu; Shan, Qun. Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose. Biochemical Pharmacology. 2007-10-01, 74 (7): 1078–1090. ISSN 0006-2952. PMID 17692828. doi:10.1016/j.bcp.2007.07.007. 
  16. ^ Jin, Yong-Ri; Jin, Jing-Ling; Li, Cheng-Hao; Piao, Xi-Xu; Jin, Nan-Ge. Ursolic acid enhances mouse liver regeneration after partial hepatectomy. Pharmaceutical Biology. 2012-04-01, 50 (4): 523–528. ISSN 1744-5116. PMID 22136205. doi:10.3109/13880209.2011.611143. 
  17. ^ Jang, Sun-Mi; Yee, Sung-Tae; Choi, Jina; Choi, Myung-Sook; Do, Gyeong-Min; Jeon, Seon-Min; Yeo, Jiyoung; Kim, Myung-Joo; Seo, Kwon-Il. Ursolic acid enhances the cellular immune system and pancreatic beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet. International Immunopharmacology. 2009-01-01, 9 (1): 113–119. ISSN 1567-5769. PMID 19013541. doi:10.1016/j.intimp.2008.10.013. 
  18. ^ Jeong, Ji-Woong; Shim, Jae-Jung; Choi, Il-Dong; Kim, Sung-Hwan; Ra, Jehyeon; Ku, Hyung Keun; Lee, Dong Eun; Kim, Tae-Youl; Jeung, Woonhee. Apple Pomace Extract Improves Endurance in Exercise Performance by Increasing Strength and Weight of Skeletal Muscle. Journal of Medicinal Food. 2015-12-01, 18 (12): 1380–1386. ISSN 1557-7600. PMID 26331671. doi:10.1089/jmf.2014.3401. 
  19. ^ Li, Songtao; Liao, Xilu; Meng, Fanyu; Wang, Yemei; Sun, Zongxiang; Guo, Fuchuan; Li, Xiaoxia; Meng, Man; Li, Ying. Therapeutic role of ursolic acid on ameliorating hepatic steatosis and improving metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease rats. PLoS One. 2014-01-01, 9 (1): e86724. ISSN 1932-6203. PMC 3906058  . PMID 24489777. doi:10.1371/journal.pone.0086724. 
  20. ^ The cytotoxic activity of ursolic acid derivatives. Eur J Med Chem. June 2005, 40 (6): 582–9. PMID 15922841. doi:10.1016/j.ejmech.2005.01.001. 

一月 01, 1970
熊果酸, 英语, ursolic, acid, 也译为乌索酸, 羟基, 熊果, 羧酸, beta, hydroxy, acid, 是一种五环三萜物质, 最早在1920年发现于苹果的表皮蜡质中, 也存在于许多植物的果皮中以及迷迭香, 麝香草等草药中, ursolic, acid, iupac名, 12ar, 14bs, hydroxy, heptamethyl, tetradecahydro, picene, carboxylic, acid, 系统名, hydroxy, heptamethylpe, ntacycl. 熊果酸 英语 Ursolic acid 也译为乌索酸 3 b 羟基 熊果 12 烯 28 羧酸 3 beta 3 hydroxy urs 12 ene 28 oic acid 是一种五环三萜物质 最早在1920年发现于苹果的表皮蜡质中 熊果酸也存在于许多植物的果皮中以及迷迭香 麝香草等草药中 Ursolic acid IUPAC名 1S 2R 4aS 6aR 6aS 6bR 8aR 10S 12aR 14bS 10 Hydroxy 1 2 6a 6b 9 9 12a heptamethyl 2 3 4 5 6 6a 7 8 8a 10 11 12 13 14b tetradecahydro 1H picene 4a carboxylic acid 1 系统名 1R 2S 5S 8R 9S 10S 14R 15R 18S 20R 18 hydroxy 1 2 8 9 15 19 19 heptamethylpe ntacyclo 12 8 0 02 11 05 10 015 20 docos 11 ene 5 carboxylic acid 1R 2S 5S 8R 9S 10S 14R 15R 18S 20R 1 2 8 9 15 19 19 七甲基 18 羟基五环 12 8 0 02 11 05 10 015 20 11 二十二烯 5 甲酸 别名 Prunol Malol beta Ursolic acid NSC4060 CCRIS 7123 TOS BB 0966 3 beta hydroxyurs 12 en 28 oic acid 1 识别 CAS号 77 52 1 Y PubChem 64945 ChemSpider 58472 SMILES O C O C 54 C H C3 C C C H 1 C CC C H 2 C 1 C CC C H O C2 C C C C 3 C CC4 C H C C H C CC5 InChI 1 C30H48O3 c1 18 10 15 30 25 32 33 17 16 28 6 20 24 30 19 18 2 8 9 22 27 5 13 12 23 31 26 3 4 21 27 11 14 29 22 28 7 h8 18 19 21 24 31H 9 17H2 1 7H3 H 32 33 t18 19 21 22 23 24 27 28 29 30 m1 s1 InChIKey WCGUUGGRBIKTOS GPOJBZKABB ChEBI 9908 性质 化学式 C30H48O3 摩尔质量 456 7 g mol 1 熔点 285 288 C 270 K 若非注明 所有数据均出自标准状态 25 100 kPa 下 目录 1 自然发生 2 潜在的生物化学作用 3 用途 4 请参见 5 参考文献自然发生 编辑熊果酸存在于许多植物 如紫茉莉 2 以及日常生活中使用的许多水果和草药 例如苹果 罗勒 越桔 蔓越莓 接骨木花 薄荷 迷迭香 薰衣草 牛至 百里香 山楂和李子 中 苹果皮含有大量的熊果酸以及相关化合物 3 潜在的生物化学作用 编辑已经研究了熊果酸的许多潜在生化作用 但是没有临床研究表明它对人类健康有益 在体外 熊果酸通过抑制STAT3激活途径抑制各种类型癌细胞的增殖 4 5 并且还可以减少癌细胞的增殖并诱导细胞凋亡 6 熊果酸也已显示能抑制JURK白血病T细胞的JNK表达和IL 2活化 导致增殖和T细胞活化的减少 7 熊果酸是一种弱芳香酶抑制剂 IC50 32mM 8 并且已经显示当添加到喂养给小鼠的饮食中时增加肌肉和棕色脂肪的量并减少白色脂肪肥胖和相关病症 在生理浓度下 熊果酸还诱导了eryptosis 有缺陷的红细胞中的类似凋亡的细胞自杀死亡 9 已经发现它可以减少肌肉萎缩并刺激小鼠的肌肉生长 也显示出潜在的心脏保护作用 10 在小鼠中 熊果酸在坐骨神经损伤后诱导神经再生 11 熊果酸可改善多摩酸诱导的小鼠认知功能障碍 12 熊果酸可通过阻断内质网应激和IkB激酶b 核因子 kB介导的炎症通路来改善高脂饮食引起的认知障碍 13 熊果酸通过抑制p38 NF kB介导的炎症途径减轻脂多糖诱导的小鼠大脑认知功能障碍 14 熊果酸可改善认知障碍并减轻D 半乳糖诱导的衰老小鼠大脑中的氧化损伤 15 熊果酸可促进部分肝切除术后小鼠肝脏的再生 16 在以高脂饮食喂养的链脲佐菌素诱导的糖尿病小鼠中 熊果酸可增强细胞免疫系统和胰腺b细胞功能 17 UA增加骨骼肌质量 以及握力和运动能力 增强耐力 减少与肌肉萎缩发展有关的基因的表达 并减少累积疲劳和运动引起的压力的指标 18 在大鼠中 熊果酸改善了高脂饮食诱导的肝脂肪变性 并改善了高脂饮食诱导的非酒精性脂肪肝疾病的代谢紊乱 19 用途 编辑熊果酸可以在用于化妆品添加剂的植物中发现 熊果酸可以作为合成更有效的生物活性衍生物的起始材料 例如实验性抗肿瘤剂 20 请参见 编辑桦木酸 模绕酮酸 齐墩果酸参考文献 编辑 1 0 1 1 CID 64945 from PubChem Constituents of Mirabilis jalapa Siddiqui S Siddiqui B S Adil Q and Begum S Fitoterapia 1990 Volume 61 No 5 page 471 abstract 页面存档备份 存于互联网档案馆 Ursolic acid from apple pomace and traditional plants A valuable triterpenoid with functional properties Food Chem April 2017 220 477 489 PMID 27855928 doi 10 1016 j foodchem 2016 10 029 Ursolic acid inhibits nuclear factor kappaB activation induced by carcinogenic agents through suppression of IkappaBalpha kinase and p65 phosphorylation correlation with down regulation of cyclooxygenase 2 matrix metalloproteinase 9 and cyclin D1 PDF Cancer Res 2003 63 15 4375 83 2020 03 02 PMID 12907607 原始内容存档 PDF 于2013 02 21 Pathak AK Bhutani M Nair AS et al Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells Mol Cancer Res 2007 5 9 943 55 PMID 17855663 doi 10 1158 1541 7786 MCR 06 0348 Wang X Zhang F Yang L Mei Y Long H Zhang X Zhang J Qimuge Suyila Su X Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo J Biomed Biotechnol 2011 2011 419343 Full text pdf 页面存档备份 存于互联网档案馆 Kaewthawee Narawan Brimson Sirikalaya The Effects of Ursolic Acid on Cytokine Production via the MAPK Pathways in Leukemic T Cells PDF EXCLI February 2013 12 February 102 114 2020 03 02 原始内容存档 PDF 于2013 05 25 Gnoatto SC Dassonville Klimpt A Da Nascimento S Galera P Boumediene K Gosmann G Sonnet P Moslemi S Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition European Journal of Medicinal Chemistry 2008 43 9 1865 77 PMID 18192087 doi 10 1016 j ejmech 2007 11 021 Triggering of erythrocyte cell membrane scrambling by ursolic acid J Nat Prod 2011 74 10 2181 2186 PMID 21923134 doi 10 1021 np2005133 Uncoupling and antioxidant effects of ursolic acid in isolated rat heart mitochondria J Nat Prod July 2011 74 7 1640 4 PMID 21648406 doi 10 1021 np200060p Liu Biao Liu Yan Yang Guang Xu Zemin Chen Jiajun Ursolic acid induces neural regeneration after sciatic nerve injury Neural Regeneration Research 2013 09 25 8 27 2510 2519 ISSN 1673 5374 PMC 4145935 nbsp PMID 25206561 doi 10 3969 j issn 1673 5374 2013 27 002 Wu Dong mei Lu Jun Zhang Yan qiu Zheng Yuan lin Hu Bin Cheng Wei Zhang Zi feng Li Meng qiu Ursolic acid improves domoic acid induced cognitive deficits in mice Toxicology and Applied Pharmacology 2013 09 01 271 2 127 136 ISSN 1096 0333 PMID 23707761 doi 10 1016 j taap 2013 04 038 Lu Jun Wu Dong mei Zheng Yuan lin Hu Bin Cheng Wei Zhang Zi feng Shan Qun Ursolic acid improves high fat diet induced cognitive impairments by blocking endoplasmic reticulum stress and IkB kinase b nuclear factor kB mediated inflammatory pathways in mice Brain Behavior and Immunity 2011 11 01 25 8 1658 1667 ISSN 1090 2139 PMID 21708244 doi 10 1016 j bbi 2011 06 009 Wang Yong Jian Lu Jun Wu Dong mei Zheng Zi hui Zheng Yuan Lin Wang Xiao hui Ruan Jie Sun Xiao Shan Qun Ursolic acid attenuates lipopolysaccharide induced cognitive deficits in mouse brain through suppressing p38 NF kB mediated inflammatory pathways Neurobiology of Learning and Memory 2011 09 01 96 2 156 165 ISSN 1095 9564 PMID 21496491 doi 10 1016 j nlm 2011 03 010 Lu Jun Zheng Yuan Lin Wu Dong Mei Luo Lan Sun Dong Xu Shan Qun Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D galactose Biochemical Pharmacology 2007 10 01 74 7 1078 1090 ISSN 0006 2952 PMID 17692828 doi 10 1016 j bcp 2007 07 007 Jin Yong Ri Jin Jing Ling Li Cheng Hao Piao Xi Xu Jin Nan Ge Ursolic acid enhances mouse liver regeneration after partial hepatectomy Pharmaceutical Biology 2012 04 01 50 4 523 528 ISSN 1744 5116 PMID 22136205 doi 10 3109 13880209 2011 611143 Jang Sun Mi Yee Sung Tae Choi Jina Choi Myung Sook Do Gyeong Min Jeon Seon Min Yeo Jiyoung Kim Myung Joo Seo Kwon Il Ursolic acid enhances the cellular immune system and pancreatic beta cell function in streptozotocin induced diabetic mice fed a high fat diet International Immunopharmacology 2009 01 01 9 1 113 119 ISSN 1567 5769 PMID 19013541 doi 10 1016 j intimp 2008 10 013 Jeong Ji Woong Shim Jae Jung Choi Il Dong Kim Sung Hwan Ra Jehyeon Ku Hyung Keun Lee Dong Eun Kim Tae Youl Jeung Woonhee Apple Pomace Extract Improves Endurance in Exercise Performance by Increasing Strength and Weight of Skeletal Muscle Journal of Medicinal Food 2015 12 01 18 12 1380 1386 ISSN 1557 7600 PMID 26331671 doi 10 1089 jmf 2014 3401 Li Songtao Liao Xilu Meng Fanyu Wang Yemei Sun Zongxiang Guo Fuchuan Li Xiaoxia Meng Man Li Ying Therapeutic role of ursolic acid on ameliorating hepatic steatosis and improving metabolic disorders in high fat diet induced non alcoholic fatty liver disease rats PLoS One 2014 01 01 9 1 e86724 ISSN 1932 6203 PMC 3906058 nbsp PMID 24489777 doi 10 1371 journal pone 0086724 The cytotoxic activity of ursolic acid derivatives Eur J Med Chem June 2005 40 6 582 9 PMID 15922841 doi 10 1016 j ejmech 2005 01 001 取自 https zh wikipedia org w index php title 熊果酸 amp oldid 69630235, 维基百科，wiki，书籍，书籍，图书馆，

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